Joshua Stein, general counsel for San Francisco-based human resources software company Zenefits, is half-coach, half-soldier. Literally.

Stein joined the Army in 1992, fresh out of college, looking forward to a 20-year career complete with what gets shown in commercials—“jumping out of airplanes, running around in the woods, firing off weapons systems,” he said. But a drawn-down army, lessened in ranks following the end of the Cold War, Stein said, proved less exciting.

So, after four years of being a soldier, he became a coach. Or a ski instructor, at least, in Colorado.

Then, inspired by his uncle, a criminal defense attorney, Stein went to law school.

More than 15 years later, Stein has served as a judge's clerk, an assistant U.S. attorney, a senior associate at Quinn Emanuel Urquhart & Sullivan, an associate general counsel for private military company Blackwater USA and general counsel at OptumRx.

In 2015, he joined Zenefits as its general counsel, but was promoted to chief compliance officer in February 2016, in response to the company's insurance licensing scandal. Some of the company's insurance sales reps were found to be unlicensed—in violation of the law in California and other states.

In the wake of the scandal, former chief executive Parker Conrad was ousted, scores of employees were let go and incoming CEO David Sacks promised a new company.

Stein helped the company settle with multiple states' insurance departments and, in November 2016, became GC again.

The Recorder recently sat down with Stein to discuss his company's response to its licensing issues last year, project management and leadership skills, and what Stein values in outside counsel. The following interview has been edited for clarity and length.

The Recorder: How big is the legal department?

Joshua Stein: [We have] 14 positions, 10 are filled and we're hiring for four. It's [all] legal and compliance. The legal folks are all lawyers. There's no paralegals, no assistants, no overhead like that. It's six lawyer positions and eight compliance positions.

TR: That's a beefed up compliance team. Has it always been that way?

JS: No. Our first full-time compliance positions started in February 2016.

TR: And it was a response, essentially, to the firing of Parker Conrad and other regulatory issues?

JS: Yes, it was. That's when I was named chief compliance officer. That was the first compliance position. But it's also something that's driven [our company]. Our product is highly regulated and covers such a broad waterfront. Benefits—both insurance and noninsurance—[are] complexly regulated on state and federal level. Payroll—complexly regulated, with tie-ins on regulations on federal and state level. And then HR and employment—again, highly complex, both federal and state components so, our folks are not just compliance like you think about in companies where they focus on the company's behavior. Here, they're very much focused on product, and that's part of what makes it so fun to work here as a legal compliance professional. You have really deep input into the product.

TR: Can you lead me through what the company experienced beginning in February 2016, when there was this flurry of activity to steer the ship, get settlements with state insurance departments and get back to operating in those states really quickly?

JS: We never stopped operating in any state. There's been no action to restrict our ability to operate in any state, and we're proud of those outcomes. The departments of insurance were tough but very fair, and they recognized that we did an extraordinary level of remediation. We reconstituted our board of directors, we changed our executive leadership, we were transparent and open with our regulators, we engaged a third-party national consulting firm to give an exhaustive report on prior compliance issues. We fixed all those issues.

Not only did we put in place these high-tech controls, but we open sourced them. It's called Licensing Plus, it's available to anybody in the industry. Our compliance folks created a software package as a free app on the Salesforce app exchange so that any carrier or any broker agency that uses Salesforce can use [the] open source, free app to enforce licensing controls with all their insurance producers.

It was developed by our own staff here. Several national insurance carriers are using it … And I think what's really important though is we got through that and we did it in a way that allowed the business to continue to operate and focus on being the business. From the legal department's point of view, we're dealing with all this fallout, but from a business point of view, the business didn't pause.

TR: If you're hiring a firm for a new matter, what separates all the teams from the rest of the, say, Harvard grads?

JS: The usual is deep expertise in the law, really good analytical skills, et cetera, et cetera, but the things that are maybe unusual, or things that maybe that outside counsel don't think enough about— one is project management skills. I'll give you an example. Our primary insurance regulatory counsel is [Orrick, Herrington & Sutcliffe] partner Tom Welsh and his team. On March 1, 2016, we delivered to all 51 state departments of insurance, 50 states and D.C., each one got—[these are] several hundred pages—got an individualized, customized report. That national accounting firm had gone and reviewed all the transactions that had taken place for the prior two years and analyzed them. It was a report on those transactions, the methodologies they used, in-depth [information] on the company and what happened. Those are very complex reports. To assemble all that and get that all out the door in one day is a huge logistical undertaking, and Orrick did a fantastic job.

Project management probably isn't the right term, leadership is the right term. You always have different groups on any project, you've got outside legal, in-house legal, other folks inside the company, and keeping all those wheels turning and having them work efficiently so you get high quality output on time, is a lot harder than it seems.

TR: How do you screen for that leadership quality when trying to find a new firm?

JS: You can get a good sense of it just by asking them about some matters they handled before and how they organized [them]. I'll see it other ways—how well do they delegate? When I go to a meeting, is there an agenda distributed ahead of time? Do we know all the action items from the last meeting and what their status is?

For instance, internally here, there's a punch list, there's an agenda for every meeting, and if there's not, we don't meet. And then after every meeting, we track the action items and we see where we are.

A lot of times things won't happen. Everybody's got 10 pounds in a five-pound bag, but the only way that you do a good job is by ruthlessly prioritizing what you do do, and what you don't do, and you can't do that if you're not tracking what's on everyone's plate. That sounds very basic, but you'd be surprised how many people don't do it. I'd say the two greatest management tools are, one is a checklist or punch list, and the other is a huddle. When things were hot and heavy, we were meeting every single day, and I would put everybody on the call. Not just the partner at the law firm. Everyone on their team, who is participating in that matter, should be on that call …It's very empowering. It improves morale with those associates where they're on the call with the client.

Contact David Ruiz at [email protected]